The lethal injection came three decades after a double-killing officials say was fueled by racial hatred, and is believed to be the first time in the modern era that Florida executed a white person convicted and sentenced to death for killing a black person.

In another milestone, Florida executed convicted killer Mark Asay with a drug never before used in a lethal injection.

Asay, who was convicted in the 1988 of killing Robert Lee Booker and Robert McDowell the previous year, was pronounced dead at 6:22 p.m. Thursday, according to the Associated Press. The AP reported that about a minute after the first drug was administered, his feet jerked and his mouth opened, and within a minute or two he was motionless.

In court documents, state officials say Asay shot and killed both men after he spent a night out drinking, using racial slurs to describe one of them. Court documents also say Asay’s cellmate testified that Asay admitted to shooting the men, used a racial slur and had white power and swastika tattoos.

Attorneys for Asay appealed to the U.S. Supreme Court, arguing that a key fact about the case has been misstated, but the justices on Thursday afternoon rejected their request for a stay.

Asay’s attorneys say that during his trial, “the prosecution’s theory of the case was that the victims were killed because of racial animus toward blacks.”

When the Florida Supreme Court in 1991 denied Asay’s appeal, the court issued an opinion incorrectly identifying McDowell, one of the victims, as a black man. However, Asay’s attorneys note, this was incorrect, which the state Supreme Court acknowledged in another opinion earlier this month, stating that McDowell — who was also known as Renee Torres — was identified as white and Hispanic. In that opinion, the Florida Supreme Court again denied Asay’s appeal.

Asay’s attorneys say the top Florida court did not consider “the central role the victim’s race had played in the case,” and they asked the U.S. Supreme Court for a stay of execution to consider the issue.

On Thursday afternoon, a little more than two hours before Asay’s scheduled execution, the justices released an order denying the request without explanation.

Florida officials had urged the court not to stay the execution, saying that despite questions regarding McDowell’s race, “there is no dispute about the race of the first victim or Asay’s racially charged statements made during the murder of that first victim.”

According to a filing from the office of Pam Bondi, the Florida attorney general, Asay used a racial slur to refer to Booker before and after killing him. Bondi’s office also noted that “regardless of his motivation, Asay murdered two different people in separate incidents that night.”

Asay told News4Jax, a North Florida news outlet, that he shot McDowell while “having a meltdown” but denied killing Booker. He also said he is not a white supremacist and only got the tattoos to blend in while incarcerated in Texas.

Since the U.S. Supreme Court reinstated the death penalty in 1976, Florida has executed 93 inmates including Asay, trailing only three states — Texas, Virginia and Oklahoma — over that span, according to the Death Penalty Information Center, a Washington-based nonprofit. In recent years, as some states have scrapped the death penalty or halted executions due to legal or logistical issues, Florida has been among the exceptions. With Asay’s execution, Florida joins Texas as the only two states to have executed a person during each of the last 10 years.

During the modern era, Florida had executed 56 white death-row inmates before Asay, and none had been executed for killing any black victims, said Robert Dunham, executive director of the Death Penalty Information Center.

Florida’s death penalty has been in limbo since January 2016, when the U.S. Supreme Court struck down its statute in the case Hurst v. Florida. The justices said Florida’s sentencing scheme gave judges, not juries, too much power.

The Hurst ruling in January 2016 also threw into doubt the status of scores of death sentences in a state with the country’s second-largest death row. In a ruling last December, the Florida Supreme Court said the Hurst case could apply retroactively to certain cases in the state, potentially clearing the way for as many as 200 death-row inmates to be able to apply for new sentences due to the Hurst decision.

Some death sentences have already been vacated. And in Florida, matching a trend nationwide, the state’s death row population has declined, falling to 362 inmates as of Thursday from 389 in 2016.

Asay’s attorneys had said the state’s new death penalty statute should be applied to him, because the jury that found him guilty recommended a death sentence by a vote of 9-3, but his stay request was denied by the Florida Supreme Court earlier this month. The same court had previously said Asay was not eligible for new sentencing, because the justices ruled that the Hurst decision would not apply retroactively to death sentences — such as Asay’s — that predated a 2002 U.S. Supreme Court ruling focused on Arizona’s death penalty.

Florida on Thursday also again broke new ground with its choice of lethal-injection drugs, becoming the latest state to alter its execution protocols amid an ongoing drug shortage.

In January, Florida adopted a new lethal-injection protocol that included etomidate, an anesthetic that experts say was never before used for an execution. The state also injected Asay with rocuronium bromide and potassium acetate, both of which have been used in executions, though the latter was used inadvertently in at least one case.

The new drug used Thursday had prompted criticism from a division of Johnson & Johnson, the pharmaceuticals giant, which said it did “not condone the use of our medicines in lethal injections for capital punishment.” Johnson & Johnson does not sell the drug — invented by scientists for the company — in the United States, and it is now made by multiple generic manufacturers.

But the company’s statement adds it to the extended list of pharmaceutical companies denouncing the use of medical drugs for lethal injections. Pfizer last year tightened restrictions on its drugs to keep them away from executions, and other companies have spoken out or gone to court to prevent their chemicals from being used to carry out death sentences. These objections have helped prompt a shortage of lethal-injection drugs across the country, which in turn has prompted a scramble in states seeking to carry out executions.

Florida had changed its drug protocol before and, in 2013, became the first state to use midazolam, a sedative, as part of an execution. The drug’s use in lethal injections became controversial, particularly after it was utilized in unusually long or bungled executions in Ohio, Oklahoma and Arizona. The U.S. Supreme Court in 2015 upheld the use of midazolam in executions, but questions and controversy have lingered, which occurred after inmates appeared to move during recent executions in Arkansas and Alabama.

U.S. Supreme Court Justice Sonia Sotomayor, in a dissent earlier this year, pilloried the use of the sedative, writing that “with respect to midazolam-centered protocols, prisoners executed by lethal injection are suffering horrifying deaths beneath a ‘medically sterile aura of peace.’ ”

Under Florida’s new lethal-injection protocol, which went into effect on Jan. 1, the drug etomidate replaces midazolam.

“The Florida Department of Corrections follows the law and carries out the sentence of the court, as laid out in Florida Statute,” the corrections department said in a statement before the execution. “This is the department’s most solemn duty, and the foremost objective with the lethal injection procedure is a humane and dignified process.”

This story was first published at 12:06 p.m. and was updated with news of the execution being carried out.

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